Potassium Carbonate → HCID 59625790, compound

HRID 2362059Notes

Reaction equation

HRID 2362059 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([N:14]1[CH2:17][CH:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[S:27][CH:28]=[CH:29][N:30]=4)=[O:25])[CH2:20][CH2:19]3)[CH2:15]1)=[O:13])=[CH:7]2.C([O-])([O-])=O.[K+].[K+]>CCO.O.C(Cl)Cl.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]>[C:2]1([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([N:14]2[CH2:15][CH:16]([N:18]4[CH2:19][CH2:20][N:21]([C:24]([C:26]5[S:27][CH:28]=[CH:29][N:30]=5)=[O:25])[CH2:22][CH2:23]4)[CH2:17]2)=[O:13])=[CH:7]3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 59625780HCID 59625780, compound

Product 1

HCID 59625790HCID 59625790, compoundYield 116%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of compound 313 (48 mg, 0.1 mmol), compound 12a (24 mg, 0.2 mmol), K2CO3 (27 mg, 0.2 mmol) and Pd(dppf)Cl2.CH2Cl2 (4 mg, 0.005 mmol) in EtOH (1 mL) and H2O (0.2 mL) was heated in a microwave reactor at 130° C. for 30 min. The reaction mixture was cooled to room temperature, diluted with CH2Cl2, and washed with H2O. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave compound 338 (28 mg). 1H NMR (400 MHz, CD3OD): δ 8.20 (d, J=1.6 Hz, 1H), 7.93 (t, J=9.6 Hz, 2H), 7.88 (d, J=3 Hz, 1H), 7.66-7.43 (m, 9H), 4.52 (bs, 1H), 4.50-4.20 (m, 4H), 4.16 (m, 1H), 3.88 (bs, 1H), 3.83 (bs, 1H), 3.28 (m, 1H), 2.60-2.40 (m, 4H). MS m/z (M+H+) 483.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b82528c4a09b4480a1b2eda02c8b5650
Source dataset
uspto-grants-2014_04
Patent number
US08691805B2

Reaction notes

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