Sodium Carbonate → HCID 86703878, compound

HRID 471438Notes

Reaction equation

HRID 471438 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20](Br)[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[Si:28]([O:35][C:36]1[CH:41]=[C:40]([CH3:42])[C:39](B(O)O)=[C:38]([CH3:46])[CH:37]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.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]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([C:39]4[C:40]([CH3:42])=[CH:41][C:36]([O:35][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:30])[CH3:29])=[CH:37][C:38]=4[CH3:46])[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 598383324-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylphenylboronic acidHCID 86703879(1S,2S)-2-[4-((R)-4-Bromo-5-cyano-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester2×

Product 1

HCID 86703878HCID 86703878, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Under nitrogen atmosphere, (1S,2S)-2-[4-((R)-4-Bromo-5-cyano-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (Intermediate 13, 590 mg, 1.38 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (0.78 g, 2.77 mmol, WO2005/63729A1), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (54 mg, 0.138 mmol), tris(dibenzylideneacetone)dipalladium(0) (63.37 mg, 0.07 mmol) and sodium carbonate (500 mg, 4.71 mmol) are suspended in 10 mL of toluene and 5 mL of water. The reaction mixture is stirred at 110° C. for 12 h then it is concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 100/01 4 80/20) to give the title compound (Yield: 500 mg).

Workup

  1. concentrationit is concentrated under vacuum
  2. customThe crude product obtained
  3. customis purified by flash chromatography (cyclohexane/ethyl acetate 100/01 4 80/20)

Sources & evidence

ORD record
ord-0f0686db68304ac185db5084c647a974
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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