HCID 67255273, compound → HCID 67255766, compound

HRID 511314Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]2[C:10]=1[CH2:9][N:8]([CH3:11])[C:7]2=[O:12]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([O:23][C:21]([N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:5]1[C:6]2[C:7](=[O:12])[N:8]([CH3:11])[CH2:9][C:10]=2[C:2]([C:14]([O:16][CH3:17])=[O:15])=[CH:3][CH:4]=1)=[O:22])([CH3:26])([CH3:27])[CH3:25]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of di-tert-butyl (7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)imidodicarbonate (Compound 118C, 500 mg, 1.13 mmol), Pd(PPh3)4 (131 mg, 0.113 mmol), in MeOH (5 mL) and THF (10 mL) was evacuated and refilled with carbon monoxide (3×), then heated at 65° C. overnight. The solvent was removed in vacuo and the crude product was taken up in EtOAc and washed successively with water then brine. The desired product was purified by column chromatography. MS (ES+): m/z 321.28 (100) [(M-Boc)H+]; HPLC: tR=1.32 min (UPLC, Analytical).

Workup

customin MeOH (5 mL) and THF (10 mL) was evacuated
additionrefilled with carbon monoxide (3×)
customThe solvent was removed in vacuo
washwashed successively with water
customThe desired product was purified by column chromatography

Sources & evidence

ORD record: ord-22781026ebb14a06a4b98f09efd38708
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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