Dichloromethane → n-{1-(Difluoromethoxy)-6-[3-(3-methoxypropyl)phenyl]-6h-benzo[c]chromen-8-yl}methanesulfonamide

HRID 1358141Notes

Reaction equation

HRID 1358141 reaction equation
[CH2:1]([O:4][CH3:5])[CH:2]=[CH2:3].B1C2CCCC1CCC2.Br[C:16]1[CH:17]=[C:18]([CH:22]2[C:31]3[CH:32]=[C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:34]=[CH:35][C:30]=3[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[O:41][CH:42]([F:44])[F:43])[O:23]2)[CH:19]=[CH:20][CH:21]=1.ClCCl.C[O-].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:44][CH:42]([F:43])[O:41][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:29]=1[C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:32][C:31]=1[CH:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:3][CH2:2][CH2:1][O:4][CH3:5])[CH:17]=1)[O:23]2

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 693921-Propene, 3-methoxy-HCID 789669-Borabicyclo(3.3.1)nonaneHCID 10278410n-[6-(3-Bromophenyl)-1-(difluoromethoxy)-6h-benzo[c]chromen-8-yl]methanesulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 10206598n-{1-(Difluoromethoxy)-6-[3-(3-methoxypropyl)phenyl]-6h-benzo[c]chromen-8-yl}methanesulfonamide

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of allylmethylether (0.015 g, 0.2 mmol) and 9-BBN (0.4 mL of 0.5M solution in THF, 0.2 mmol) was shaken for 3 hours at 65° C, cooled down to 23° C., treated with solution of Example 103 (0.05 g, 0.10 mmol), [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (0.004 g, 0.005 mmol), and sodium methoxide (0.016 g, 0.3 mmol) in THF (1 mL), shaken at 65° C. for 15 hours, cooled down to 23° C., treated with water (50 mL), and extracted with ethyl acetate(3×50 mL). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The concentrate was purified by HPLC with aqueous 0.1% TFA and CH3CN to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.15 (d, J=9 Hz, 1H), 7.07-7.56 (m, 7H), 6.87-6.92 (m, 3H), 6.25 (s, 1H), 3.24 (t, J=6 Hz, 2H), 3.14 (s, 3H), 3.01 (s, 3H), 2.56 (t, J=7 Hz, 2H), 1.72 (m, J=7 Hz, 2H); MS (ESI(−)Q1MS m/z 488 (M−H).

Workup

  1. temperaturecooled down to 23° C.
  2. extractionextracted with ethyl acetate(3×50 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by HPLC with aqueous 0.1% TFA and CH3CN

Sources & evidence

ORD record
ord-3782f15010204878ba7b15c9f37d69d7
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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