4-Methylmorpholine → Methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate

HRID 1423328Notes

Reaction equation

HRID 1423328 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[S:15][CH:16]=1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:11][C:12]2[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[S:15][CH:16]=2)=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 7351504-Bromopyridine-2-carboxylic acidHCID 10773224Methyl 4-aminothiophene-2-carboxylateHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 66628543Methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-pyridine-2-carboxylic acid (1.98 g, 9.80 mmol), methyl 4-aminothiophene-2-carboxylate (1.40 g, 8.91 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (4.07 g, 10.7 mmol), and N-methylmorpholine (1.18 mL, 10.7 mmol) in N,N-dimethylformamide (18 mL) was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure, the residue suspended in acetonitrile, and the solids were isolated by filtration. The solids were washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL), and dried under reduced pressure to afford methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate, a compound of formula (19) as a white powder (2.70 g, 90% yield). M+1=341.1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solids were isolated by filtration
  3. washThe solids were washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-121c4f2c1bae4210bc242b6e9ff6a80c
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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