Sodium Carbonate → Phenyl Methylcarbamate

HRID 1965862Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2SC(NCCF)=N[C:6]=2[CH:14]=1.[CH3:15][N:16](C1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1)[C:17](=[O:23])[O:18]C(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.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:6]1([O:23][C:17](=[O:18])[NH:16][CH3:15])[CH:5]=[CH:4][CH:3]=[CH:2][CH:14]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 5-Bromo-N-(2-fluoroethyl)benzo[d]thiazol-2-amine (60 mg, 0.2 mmol), tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (68 mg, 0.2 mmol), and tetrakis(triphenylphosphine)palladium (11 mg, 0.01 mmol) in 2 mL dioxane and 0.5 mL of a 1 M Na2CO3 aqueous solution was heated at 95° C. in a microwave reactor for 10 min. After cooling to rt, it was diluted with EtOAc (30 mL) and washed with brine (30 mL), dried over MgSO4 and concentrated. The crude product was purified with silica chromatography (5% to 50% EtOAc in hexane) to afford tert-butyl 44242-fluoroethylamino)benzo[d]thiazol-5-yl)phenyl(methyl)carbamate as a white solid (60 mg, 75%). MS (ESI) m/z 402 (M+H+).

Workup

temperatureAfter cooling to rt
washwashed with brine (30 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified with silica chromatography (5% to 50% EtOAc in hexane)

Sources & evidence

ORD record: ord-7ad714ba15ed4c279d69970bba9119d1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420052B2

Reaction notes

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