tert-Butyl 2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylate → 1,4,4-Trimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,1-benzoxazin-2-one

HRID 2209292Notes

Reaction equation

HRID 2209292 reaction equation
O=[C:2]1[C:10]2(CCN(C(OC(C)(C)C)=O)C[CH2:11]2)[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)N1.BrC1C=CC2C(C)(C)[O:40][C:39](=[O:44])[N:38](C)[C:37]=2C=1>>[CH3:37][N:38]1[C:4]2[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][C:9]=2[C:10]([CH3:11])([CH3:2])[O:44][C:39]1=[O:40]

Participants

3

Reactant 2

HCID 92133768tert-Butyl 2-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylateHCID 1178431767-Bromo-1,4,4-trimethyl-3,1-benzoxazin-2-one

Product 1

HCID 1234331871,4,4-Trimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,1-benzoxazin-2-one

Procedure

Following the procedure described for intermediate 7.33 (Step 2), starting from 7-bromo-1,4,4-trimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.38 (540 mg), 560 mg of 1,4,4-trimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d][1,3]oxazin-2(4H)-one 7.40 was obtained. LCMS [M+H]+: 318.12.

Sources & evidence

ORD record
ord-bf837b757c2a47638ca9a440e05347e8
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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