Tricyclohexylphosphine → 2-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097435Notes

Reaction equation

HRID 2097435 reaction equation
Br[C:2]1[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[CH:6]=[N:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:28][CH3:29].BrC1N(COCC[Si](C)(C)C)C2C=NN(COCC[Si](C)(C)C)C(=O)C=2C=1C.[F:58][CH:59]([F:82])[O:60][C:61]1[CH:62]=[CH:63][C:64](B2OC(C)(C)C(C)(C)O2)=[C:65]2[C:70]=1[O:69][C:68]([CH3:72])([CH3:71])[CH:67]=[CH:66]2.C1(OC2C=C(B3OC(C)(C)C(C)(C)O3)C=CC=2OC(F)F)CC1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>>[F:82][CH:59]([F:58])[O:60][C:61]1[CH:62]=[CH:63][C:64]([C:2]2[N:19]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:5]3[CH:6]=[N:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:16])[CH3:17])[C:9](=[O:10])[C:4]=3[C:3]=2[CH2:28][CH3:29])=[C:65]2[C:70]=1[O:69][C:68]([CH3:71])([CH3:72])[CH:67]=[CH:66]2

Participants

6

Reactant 5

HCID 75806TricyclohexylphosphineHCID 666026762-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 666027042-Bromo-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028342-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 666029032-Bromo-3-ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666025822-(8-Difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-3-ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 101.3%

Procedure

Reaction and post treatment were carried out in the same manner as in Example 4-(a) except for using 794 mg (1.57 mmol) of 2-bromo-3-ethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in the following Reference example 19-(d) in place of 2-bromo-3-methyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one, using 1.08 g (3.06 mmol) of 2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane obtained in the following Reference example 1-(i) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, and using 57 mg of tricyclohexylphosphine in place of butyl-di-1-adamantylphosphine, whereby 1.03 g of the title compound was obtained as a brownish oil substantially quantitatively.

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-d93fcc4394d4496b842caa3e81f6cf6d
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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