Cesium carbonate → HCID 58552862, compound

HRID 520454Notes

Reaction equation

HRID 520454 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[C:11]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[O:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[B-](F)(F)(F)[CH2:70][N:71]1[CH2:75][CH2:74][CH2:73][CH2:72]1.[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:18][N:17]1[C:16](=[O:19])[C:15]2[C:10](=[C:11]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[O:21])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([CH2:70][N:71]2[CH2:75][CH2:74][CH2:73][CH2:72]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 45588176Potassium trifluoro[(pyrrolidin-1-yl)methyl]borateHCID 58552853HCID 58552853, compound

Product 1

HCID 58552862HCID 58552862, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Degassed THF/H2O (4 mL, 10:1) was added to a microwave vial containing 2-(4-bromophenyl)-3-methyl-4-oxo-N-(pyridin-2-yl)-3,4-dihydroquinazoline-8-carboxamide 28 (100 mg, 0.23 mmol), Cs2CO3 (224 mg, 0.69 mmol), Pd(OAc)2 (1.5 mg, 0.007 mmol), XPHOS (65 mg, 0.014 mmol), and potassium 1-trifluoroboratomethylpyrrolidine (48 mg, 0.25 mmol). The reaction mixture was heated at 150° C. in a microwave reactor for 30 min., poured into H2O and extracted with EtOAc. The combined organics were washed with brine, dried, concentrated and the crude residue purified by MPLC eluting with CH2Cl2/MeOH (0-10%) to give Compound 275 (63 mg, 63% yield). MS (ESI) calc. for C26H25N5O2: 439.20. found: 440 [M+H].

Workup

  1. customDegassed THF/H2O (4 mL, 10:1)
  2. additionwas added to a microwave
  3. extractionextracted with EtOAc
  4. washThe combined organics were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customthe crude residue purified by MPLC
  8. washeluting with CH2Cl2/MeOH (0-10%)

Sources & evidence

ORD record
ord-5633d2f86e694a4185024f6c053a5484
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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