HCID 71258011, compound → HCID 71257872, compound

HRID 337311Notes

Reaction equation

HRID 337311 reaction equation
[C:1]([NH:5][C:6](=[O:20])[C:7]1[C:12]([CH2:13]O)=[CH:11][C:10]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][C:8]=1[F:19])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:15]([C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([C:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:20])=[C:8]([F:19])[CH:9]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 71258011HCID 71258011, compound

Product 1

HCID 71257872HCID 71257872, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N,4-di-tert-butyl-2-fluoro-6-(hydroxymethyl)benzamide (4.3 g, 15.3 mmol, Eq: 1.00) in MeOH (100 ml) was added Pd—C 10% (50% wet) (1.19 g) and the reaction mixture was stirred under H2 atmosphere (balloon) for 3 h. Reaction mixture was filtered over a celite pad and the celite pad washed with EtOH(3×50 mL). The combined filtrate and washes were evaporated under vacuum to give 4.01 g of product as a white solid (99% yield); LC/MS, m/z 266[M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (s, 9 H) 1.48 (s, 9 H) 2.41 (s, 3 H) 5.60 (br. s., 2 H) 6.90-6.95 (m, 1 H) 7.00 (d, J=0.51 Hz, 1 H).

Workup

  1. customReaction mixture
  2. filtrationwas filtered over a celite pad
  3. washthe celite pad washed with EtOH(3×50 mL)
  4. customThe combined filtrate and washes were evaporated under vacuum

Sources & evidence

ORD record
ord-5ba3091ea29c4a87a2e5cbffe4aa10ab
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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