Potassium Carbonate → HCID 66563617, compound

HRID 1051182Notes

Reaction equation

HRID 1051182 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:21]=[CH:20][C:13]([C:14]([NH:16][CH:17]4[CH2:19][CH2:18]4)=[O:15])=[C:12]([CH3:22])[CH:11]=3)[C:6]=2[CH:23]=1.[N:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:17]1([NH:16][C:14](=[O:15])[C:13]2[CH:20]=[CH:21][C:10]([N:7]3[C:6]4[CH:23]=[C:2]([C:34]5[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=5)[CH:3]=[C:4]([NH:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:5]=4[N:9]=[CH:8]3)=[CH:11][C:12]=2[CH3:22])[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 68386507HCID 68386507, compound

Product 1

HCID 66563617HCID 66563617, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of 4-{6-bromo-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}-N-cyclopropyl-2-methylbenzamide (30.8 mg, 0.05 mmol) in NMP (2 mL) was subsequently added 24.58 mg pyridin-4-ylboronic acid (0.2 mmol, 4 eq), 12.3 mg Pd(dppf)Cl2 (0.015 mmol, 0.3 eq) and aqueous potassium carbonate solution (1M, 150 μL) in one portion at rt. After heating for 40 min at 140° C. in a microwave oven, the mixture was filtered an subjected to preparative HPLC to yield 6.77 mg (27.95%) N-cyclopropyl-2-methyl-4-{6-(pyridin-4-yl)-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}benzamide.

Workup

  1. customat rt
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-2f44e53de9f948a0b3d00540e987a50e
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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