Potassium Phosphate, Tribasic → HCID 67017338、化合物

HRID 1842040ノート

反応式

HRID 1842040 の反応式
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

参加物

11

反応物 7

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54421415HCID 54421415、化合物HCID 67017336HCID 67017336、化合物HCID 866651331201684-65-2HCID 135926475HCID 135926475、化合物

生成物 1

HCID 67017338HCID 67017338、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cada0dc8e60a42c0836481175c93eb75
出典データセット
uspto-grants-2015_02
特許番号
US08946212B2

反応ノート

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