Water → Ethyl 3-(3-{1-(difluoromethoxy)-8-[(methylsulfonyl)amino]-6h-benzo[c]chromen-6-yl}phenyl)propanoate

HRID 1358142Notes

Reaction equation

HRID 1358142 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[CH:18]=[C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:21][C:16]=3[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:27][CH:28]([F:30])[F:29])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[Br-].[CH2:32]([O:34][C:35](=[O:39])[CH2:36][CH2:37][Zn+])[CH3:33].O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[F:29][CH:28]([F:30])[O:27][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:18][C:17]=1[CH:8]([C:4]1[CH:3]=[C:2]([CH2:37][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:39])[CH:7]=[CH:6][CH:5]=1)[O:9]2

Participants

6

Reactant 3

HCID 962WaterHCID 10278410n-[6-(3-Bromophenyl)-1-(difluoromethoxy)-6h-benzo[c]chromen-8-yl]methanesulfonamideHCID 178471816HCID 178471816, compound

Product 1

HCID 10229635Ethyl 3-(3-{1-(difluoromethoxy)-8-[(methylsulfonyl)amino]-6h-benzo[c]chromen-6-yl}phenyl)propanoate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 103 (0.05 g, 0.10 mmol), tetrakis(triphenylphosphine) palladium(O) (0.01, 0.01 mmol), and 3-ethoxy-3-oxopropylzincbromide (0.6 ml of 0.5M solution in THF) in THF (2 mL) was shaken in a sealed tube at 80° C. for 15 hours, treated with water (2 mL), and extracted with ethyl acetate. The extract was the concentrated and the residue was purified by high throughput HPLC with aqueous 0.1% TFA and CH3CN to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.17 (d, J=9 Hz, 1H), 6.52-7.74 (m, 10H), 6.31 (s, 1H), 4.18 (q, J=7 Hz, 2H), 3.02 (s, 3H), 1.25 (t, J=7 Hz, 3H); MS (ESI(−)Q1MS m/z 516 (M−H).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. customthe residue was purified by high throughput HPLC with aqueous 0.1% TFA and CH3CN

Sources & evidence

ORD record
ord-7ad60d88b6c54635a92719b42af713c5
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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