Dimethylformamide → HCID 90313085, compound

HRID 1523982Notes

Reaction equation

HRID 1523982 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[C:16]([OH:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=2[F:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 136499151HCID 136499151, compound

Product 1

HCID 90313085HCID 90313085, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-ol Example 476 (50 mg, 0.18 mmol) and DMF (1 mL) was added Cs2CO3 (116 mg, 0.36 mmol). The mixture was stirred at rt for 30 min. Methyl 2-bromoacetate (30 mg, 0.19 mmol) was added and the resultant mixture stirred at rt for 1 hour and then poured into 15 mL of water. The precipitate was collected and washed with water and air dried to give methyl 2-((4′-(5-aminopyrazin-2-yl)-3′-fluoro-[1,1′-biphenyl]-2-yl)oxy)acetate (50 mg, 72%). MS (ESI): mass calcd. for C19H16FN3O3, 353.12; m/z found, 354.0 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.03 (s, 1H), 7.93 (m, 1H), 7.57 (d, J=13.0, 1H), 7.54 (d, J=9.2, 1H), 7.50 (d, J=7.4, 1H), 7.34 (m, 1H), 7.10-7.02 (m, 2H), 6.70 (s, 2H), 4.89 (s, 2H), 3.71 (s, 3H).

Workup

  1. customThe precipitate was collected
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-a320f9d43cb54cd3b57e4c8ec1c02f63
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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