Sodium Bicarbonate → HCID 10300704, compound

HRID 1358139Notes

Reaction equation

HRID 1358139 reaction equation
[F:1][CH:2]([F:25])[O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][C:7]=1[CH:8](OC)[O:9]2.[Br-].[Br:27][C:28]1[S:32][C:31]([Zn+])=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+]>ClCCl>[Br:27][C:28]1[S:32][C:31]([CH:8]2[C:7]3[CH:16]=[C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH:18]=[CH:19][C:6]=3[C:5]3[C:10](=[CH:11][CH:12]=[CH:13][C:4]=3[O:3][CH:2]([F:25])[F:1])[O:9]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18504029HCID 18504029, compoundHCID 178419757HCID 178419757, compound

Product 1

HCID 10300704HCID 10300704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 96C (50 mg, 0.13 mmol) in dichloromethane (20 ml) at −20° C. was treated with borontrifluoridediethyletherate (184 mg, 1.3 mmol) dropwise, stirred for 5 minutes, treated with 5-bromo-2-thienylzincbromide (7.8 ml of 0.5M solution in THF, 3.9 mmol) dropwise over 2 minutes, stirred for 15 minutes, treated with saturated NaHCO3 solution (15ml), extracted with dichloromethane. The extract was concentrated and the concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product. MS (ESI(−)Q1MS) m/z 500 and 502 (M−H)−; 1H NMR (400 MHz, CD3OD) δ 8.29 (d, J=9 Hz, 1H), 7.32 (dd, J=9 Hz, 2 Hz, 1H), 7.21(t, J=9 Hz, 1H), 7.16 (d, J=2 Hz, 1H), 6.88 (t, J=74 Hz, 1H), 6.84-6.89 (m, 3H), 6.59 (dd, J=4 Hz, 1Hz, 1H), 6.39 (s, 1H), 3.01 (s, 3H).

Workup

  1. stirringstirred for 15 minutes
  2. extractionextracted with dichloromethane
  3. concentrationThe extract was concentrated
  4. customthe concentrate was purified by flash column chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-d00f9eb776c441d5b866572913d54281
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

Loading…