2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 66580819, compound

HRID 1521828Notes

Reaction equation

Br[C:2]1[C:7]2[S:8][CH2:9][C:10]3[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:11]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[CH3:55][N:56](C=O)C.O>C(Cl)Cl.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:55]([C:2]1[C:7]2[S:8][CH2:9][C:10]3[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:11]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:56]

Participants

Conditions

Temperature: 120 °C

Procedure

Ethyl 6-bromo-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylate (200 mg, 0.483 mmol) in DMF/water (10:1, 4.4 mL) is taken in a sealed tube and purged with nitrogen for 10 min. Zinc cyanide (64 mg, 0.545 mmol), Pd2 (dba)3 (18 mg, 0.019 mmol) and s-phos (20 mg, 0.483 mmol) are then added and heated to 120° C. for 2 h. After this time, the reaction mixture is diluted with DCM, filtered through acelite pad, washed with water, dried over Na2SO4 and concentrated under reduced pressure to afford 200 mg of the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 7.74-7.72 (m, 1H), 7.60-7.55 (m, 3H), 7.48-7.46 (m, 2H), 7.18-7.14 (m, 1H), 6.91-6.89 (dd, J=1.1, 8.0 Hz, 1H), 4.40 (s, 2H), 4.36-4.31 (m, 2H), 1.33-1.29 (t, J=7.1 Hz, 3H). MS (ESI+): 362.2.

Workup

custompurged with nitrogen for 10 min
filtrationfiltered through acelite pad
washwashed with water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-725265eb81874194b74a129f437ee1f9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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