Pivaloyl chloride → N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide

HRID 2378676Notes

Reaction equation

HRID 2378676 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[CH2:16][OH:17].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:15][C:11]1[C:10]([CH2:16][OH:17])=[C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 11521092(2-Amino-6-fluorophenyl)methanol

Product 1

HCID 59732042N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylacetyl chloride (0.25 mL, 1.99 mmol) was added to a solution of (2-amino-6-fluorophenyl)methanol (268 mg, 1.90 mmol) in CH2Cl2 (10 mL) at 0° C., followed by the addition of DIEA (1.0 mL, 5.7 mmol). The mixture was stirred for 1 hr, followed by normal aqueous work-up to afford the expected crude product, N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide, as a colorless oil(415 mg, 97% yield), which was used directly in the next step; 1H NMR (400 MHz, CDCl3) δppm 1.29 (s, 9H), 2.64 (s, 1H), 4.78 (d, J=4.78 Hz, 2H), 6.75-6.84 (m, 1H), 7.23 (td, J=8.62, 5.92 Hz, 1H), 7.86 (d, J=8.31 Hz, 1H), 8.97 (s, 1H); Mass spec. 226.11 (MH+), Calc. for C12H16FNO2 225.12.

Sources & evidence

ORD record
ord-3c9a4887b2ec4c4fa8597f43479accd3
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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