Acetic Anhydride → HCID 59655846, compound

HRID 2054365Notes

Reaction equation

HRID 2054365 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([Sn:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9].[CH3:14][C:15](OC(C)=O)=[O:16].CCN(CC)CC.CCOC(C)=O.O>C(Cl)Cl>[C:15]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([Sn:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9])(=[O:16])[CH3:14]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22728543Water ethylacetateHCID 59655900HCID 59655900, compound

Product 1

HCID 59655846HCID 59655846, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-aminomethyl-4-fluoro-1-trimethylstannylbenzene (505.4 mg, 1.76 mmol), Ac2O (215.3 μL, 2.28 mmol) and NEt3 (489 μL, 3.51 mmol) was stirred at room temperature in CH2Cl2 (18 mL). After 3 h, extractive EtOAc/H2O workup followed by flash chromatography (EtOAc/Hexanes, 40:60) provided the title compound (422 mg, 73%) as an oil. 1H NMR (DMSO, 400 MHz): 8.29 (br s, 1H), 7.41 (d, J=7.52 Hz, 1H), 7.45-7.30 (m, 1H), 7.14 (dd, J=10.9, 8.2 Hz, 1H), 4.27 (d, J=5.47 Hz, 2H), 1.85 (s, 3H), 0.26 (s, 9H).

Sources & evidence

ORD record
ord-67640b3cea5347a29a57d55941ce207d
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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