2,6-Difluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenol → HCID 178467125, compound

HRID 2271709Notes

Reaction equation

HRID 2271709 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[CH:11][C:10](Br)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[F:30][C:31]1[CH:36]=[C:35](B2CC(C)(C)C(C)(C)C2)[CH:34]=[C:33]([F:46])[C:32]=1[OH:47]>>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[CH:11][C:10]([C:35]1[CH:36]=[C:31]([F:30])[C:32]([OH:47])=[C:33]([F:46])[CH:34]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 667164022,6-Difluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenolHCID 178467071HCID 178467071, compound

Product 1

HCID 178467125HCID 178467125, compoundYield 59%

Procedure

Following general procedure D, tert-butyl trans-4-(3-acetyl-6-bromoquinolin-4-ylamino)cyclohexylcarbamate (47 mg, 0.100 mmol) was reacted with 2,6-difluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenol (97 mg, 0.382 mmol) to afford the desired product (30 mg, 59%) as a yellow solid: ESI MS m/z 512 [C28H31F2N3O4+H]+.

Sources & evidence

ORD record
ord-4bc8be69b97e47d5bebb947b51a62045
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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