4-(Dihydroxyboranyl)-3-fluorobenzoic acid → HCID 57407162, compound

HRID 1472679Notes

Reaction equation

HRID 1472679 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[N:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([F:26])[CH:18]=1)([OH:16])=[O:15]>>[F:26][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1)[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 231341774-(Dihydroxyboranyl)-3-fluorobenzoic acidHCID 592548522-Chloro-6-methoxyquinazoline

Product 1

HCID 57407162HCID 57407162, compoundYield 38%

Procedure

Prepared according to Scheme 6, B conditions starting from Intermediate 8 and 4-carboxy-2-fluorophenylboronic acid, where the crude product of step 2 was purified by prep-HPLC (0.1% TFA as additive) after which most of the CH3CN was removed under reduced pressure and the remaining solvent was removed by lyophilization to give the product (40 mg, yield 38%). 1H NMR (MeOD 400 MHz): δ 9.42 (s, 1H), 8.13 (t, J=7.6 Hz, 1H), 8.02-7.95 (m, 2H), 7.86 (d, J=11.2 Hz, 1H), 7.62 (dd, J=9.2, 2.4 Hz, 1H), 7.32 (d, J=2.4 Hz, 1H). MS (ESI): m/z 284.9 [M+H]+.

Workup

  1. customPrepared
  2. customwas purified by prep-HPLC (0.1% TFA as additive) after which most of the CH3CN
  3. customwas removed under reduced pressure
  4. customthe remaining solvent was removed by lyophilization

Sources & evidence

ORD record
ord-a486c47f337c42cca22a64bb4c209fe9
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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