4-(Dihydroxyboranyl)-3-fluorobenzoic acid → HCID 67974681, compound

HRID 1472700Notes

Reaction equation

HRID 1472700 reaction equation
Cl[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.[C:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([F:30])[CH:22]=1)([OH:20])=[O:19]>>[F:30][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1)[C:18]([OH:20])=[O:19]

Participants

3

Reactant 2

HCID 231341774-(Dihydroxyboranyl)-3-fluorobenzoic acidHCID 53212388HCID 53212388, compound2×

Product 1

HCID 67974681HCID 67974681, compoundYield 19%

Procedure

Followed the coupling procedure described in Step 1 of Compound VIII-2 (Example 65), where the starting materials were 2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline (Intermediate 11) and 4-carboxy-2-fluorobezeneboronic acid. After H2O quench, the aqueous layer was acidified with 0.1M HCl to pH=1, followed by EtOAc/aqueous workup and column purification to give 3-fluoro-4-(6-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)benzoic acid (50 mg, yield 19%).

Workup

  1. customAfter H2O quench
  2. customfollowed by EtOAc/aqueous workup and column purification

Sources & evidence

ORD record
ord-7bde6921bfd4447e82be37bca492330f
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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