Trimethylboroxine → HCID 67449457, compound

HRID 1853747Notes

Reaction equation

HRID 1853747 reaction equation
Br[C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:31]=[CH:30][C:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:18]([F:32])[CH:17]=2)=[C:4]([O:33][CH3:34])[CH:3]=1.[CH3:35]B1OB(C)OB(C)O1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[F:32][C:18]1[CH:17]=[C:16]([C:5]2[C:6]3[C:7]4[CH:15]=[CH:14][S:13][C:8]=4[C:9](=[O:12])[NH:10][C:11]=3[C:2]([CH3:35])=[CH:3][C:4]=2[O:33][CH3:34])[CH:31]=[CH:30][C:19]=1[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 574072TrimethylboroxineHCID 67450568HCID 67450568, compound

Product 1

HCID 67449457HCID 67449457, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Following General Procedure I, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (300 mg, 0.55 mmol) was reacted with trimethylboroxine (207 mg, 1.65 mmol) and Pd(pph3)4 (63 mg, 0.05 mmol) to afford the desired product (155 mg, 58%) as a brown solid. ESI MS m/z 483 [C26H27FN2O4S+H]+.

Sources & evidence

ORD record
ord-dddd570836664895987f18992c8b6a39
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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