Dichloromethane → HCID 68866398, compound

HRID 1725938Notes

Reaction equation

HRID 1725938 reaction equation
Br[C:2]1[C:11]2[C:10]([CH3:12])=[CH:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])(=[O:16])=[O:15].[C:24](=[O:27])([O-])[O-:25].[Li+].[Li+].[CH2:30](Cl)Cl.[C]=O>CO.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]>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:14]([NH:13][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[C:11]=2[C:2]=1[C:24]([O:25][CH3:30])=[O:27])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11125Lithium CarbonateHCID 68863955HCID 68863955, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 68866398HCID 68866398, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

A solution of Example 275D (2.85 g) in 100 mL of methanol was treated with lithium carbonate (1.6 g) and PdCl2(dppf).CH2Cl2 (588 mg), heated to 120° C. under 500 psi carbon monoxide pressure for 16 hours, and concentrated. The residue was purified by silica gel column chromatography eluting with 10% ethyl acetate in n-hexane to yield 2.50 g of the desired product. MS (ESI(+)) m/e 393 (M+NH4)+; MS (ESI(−)) m/e 374 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.89 (s, 1H), 7.65-7.73 (m, 2H), 7.45 (t, 1H), 7.33 (t, 1H), 7.22 (d, 1H), 6.92 (d, 1H), 6.04 (br s, 1H), 3.62 (s, 3H), 2.58-2.61 (m, 2H), 2.06 (br. 2H), 1.81 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography
  3. washeluting with 10% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-b905b7fb60ab43d8af7e117c0e471eef
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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