Water → HCID 54749376, compound

HRID 1661495Notes

Reaction equation

HRID 1661495 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14]([OH:17])=[C:13]([C:18]([NH:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19])[C:12](=[O:29])[N:11]([CH3:30])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.BrC1SC2C(O)=C(C(NCC(OCC)=O)=O)C(=O)N(C)C=2C=1.FC1C=CC(B(O)O)=CC=1.O>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[C:14]([OH:17])=[C:13]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[C:12](=[O:29])[N:11]([CH3:30])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2856454-Fluorophenylboronic acidHCID 67429520HCID 67429520, compoundHCID 86631545HCID 86631545, compound

Product 1

HCID 54749376HCID 54749376, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

tert-Butyl 2-(2-(4-fluorophenyl)-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate. A mixture of ethyl 2-(2-bromo-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate (0.20 g, 0.48 mmol, Method 7), 4-fluorophenylboronic acid (0.134 g, 0.959 mmol, commercially available from Aldrich), Pd(Ph3)4 (0.055 g, 0.048 mmol) in 1,2-dimethoxyethane (4 mL) and aqueous Na2CO3 (2M, 0.72 mL) was heated under N2 at 100° C. for 2 hours. The suspension was cooled to room temperature, poured into water, extracted with CHCl3, dried over MgSO4 and evaporated. The residue was rinsed with Et2O and dried in vacuo to give the title compound. MS (ESI) m/z: Calculated 432.4; Observed; 431.1. 1H NMR (400 MHz, CDCl3) δ ppm 10.72-10.672 (1H, m), 7.53 (1H, s), 7.35-7.30 (2H, m), 7.14 (2H, t, J=8.5 Hz), 4.12 (2H, d, J=5.3 Hz), 3.23 (3H, s), 1.50 (9H, s).

Workup

  1. extractionextracted with CHCl3
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. washThe residue was rinsed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-94d19c956887409786988a3ba7a4346c
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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