3-Fluorobenzoic Acid → HCID 52913683, compound

HRID 1887454Notes

Reaction equation

HRID 1887454 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:9]=1)[C:5]#[N:6].[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=[O:22].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([F:17])[CH:19]=2)[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[N:15][CH:14]=[N:13][CH:12]=2)[CH:7]=1)#[N:6]

Participants

7

Reactant 4

HCID 99683-Fluorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67306607HCID 67306607, compound

Product 1

HCID 52913683HCID 52913683, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 22 (10 mg, 0.047 mmol, 1.2 eq), 3-fluorobenzoic acid (5.5 mg, 0.039 mmol, 1.0 eq), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (31 mg, 0.082 mmol, 2.1 eq), and N,N-Diisopropylethylamine (11 mg, 0.085 mmol, 2.1 eq) were dissolved in CH2Cl2 (0.43 mL) and DMF (0.09 mL) and stirred at rt overnight. The reaction was quenched with water, and the layers were separated via phase separation. The organic layer was dried on air concentrator and purified by flash chromatography on silica gel to give 5.5 mg (42%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.08 (s, 1H), 8.57 (s, 2H), 8.13 (s, 1H), 7.80 (s, 1H), 7.74 (s, 1H), 7.59 (dd, J=18.9, 8.4 Hz, 2H), 7.51-7.46 (m, 1H), 7.31-7.26 (m, 1H), 7.08 (s, 1H); ES-MS [M+1]+: 335.1.

Workup

  1. customThe reaction was quenched with water
  2. customthe layers were separated via phase separation
  3. customThe organic layer was dried on air concentrator
  4. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-00f9feba794c4331bee7d1ce5eaa2630
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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