7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one → 4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-3,1-benzoxazin-2-one

HRID 2209291Notes

Reaction equation

HRID 2209291 reaction equation
O=C1C2(CCN(C(OC(C)(C)C)=O)CC2)[C:9]2[C:4](=[CH:5][C:6]([B:23]3[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]3)=[CH:7][CH:8]=2)[NH:3]1.BrC1C=C[C:36]2[C:41](C)([CH3:42])[O:40][C:39](=[O:44])NC=2C=1>>[CH3:36][C:41]1([CH3:42])[O:40][C:39](=[O:44])[NH:3][C:4]2[CH:5]=[C:6]([B:23]3[O:24][C:25]([CH3:31])([CH3:30])[C:26]([CH3:28])([CH3:29])[O:27]3)[CH:7]=[CH:8][C:9]1=2

Participants

3

Reactant 2

HCID 468564867-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-oneHCID 92133768tert-Butyl 2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 1240161924,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-3,1-benzoxazin-2-one

Procedure

Following the procedure described for intermediate 7.33 (Step 2), starting from 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.37 (60 mg), 77 mg of 4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d][1,3]oxazin-2 (4H)-one 7.39 was obtained. LCMS [M+H]+: 304.19.

Sources & evidence

ORD record
ord-501a2c78f1e348fb9701daef0a042232
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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