Potassium Phosphate, Tribasic → HCID 67017338, compound

HRID 1842040Notes

Reaction equation

HRID 1842040 reaction equation
Br[C:2]1[CH:9]=[C:8]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[CH:20][CH:21]=3)[CH2:16][C:15]([CH3:34])([CH3:33])[CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].BrC1[CH:37]=[C:38]2[C:43](=CC=1)NCC(C)(C)C2.BrC1C=C(S(Cl)(=O)=O)C=CC=1C#N.ClC1C=C(N2C3C(=CC(C4C=CC(C(F)(F)F)=CC=4)=CC=3)C(C)(C)CC2)C=CC=1C1NC(=O)ON=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH:43]1([C:2]2[CH:9]=[C:8]([S:10]([N:13]3[C:22]4[C:17](=[CH:18][C:19]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=5)=[CH:20][CH:21]=4)[CH2:16][C:15]([CH3:33])([CH3:34])[CH2:14]3)(=[O:11])=[O:12])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:38][CH2:37]1

Participants

11

Reactant 7

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54421415HCID 54421415, compoundHCID 67017336HCID 67017336, compoundHCID 866651331201684-65-2HCID 135926475HCID 135926475, compound

Product 1

HCID 67017338HCID 67017338, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

90 mg 2-Bromo-4-[3,3-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-benzonitrile (derived from 6-Bromo-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline (synthesis described in WO 9629327), 4-(Trifluormethyl)phenyl-ylboronic acid and 3-Bromo-4-cyano-benzenesulfonyl chloride according to the method described for 3-{2-Chloro-4-[4,4-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-phenyl}-4H-[1,2,4]oxadiazol-5-one in example 3), 153 mg Potassium phosphate (tribasic heptahydrate) 6 mg tricyclohexylphosphine and 42 mg cyclopropylboronic acid were dissolved in a mixture of 30 ml toluene and 0.6 ml water. An argon stream was bubbled through the reaction mixture for twenty minutes. Then 7.4 mg palladium(II)acetate were added and the reaction mixture stirred under microwave irradiation at 120° C. for one hour. The cooled reaction mixture was diluted with 50 ml ethyl acetate and filtered trough a pad of celite. The filtrate was evaporated and purified by chromatography on silica gel to obtain 73 mg 2-Cyclopropyl-4-[3,3-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-benzonitrile.

Workup

  1. customAn argon stream was bubbled through the reaction mixture for twenty minutes
  2. additionThen 7.4 mg palladium(II)acetate were added
  3. customThe cooled reaction mixture
  4. filtrationfiltered trough a pad of celite
  5. customThe filtrate was evaporated
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-cada0dc8e60a42c0836481175c93eb75
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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