Dichloromethane → [4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

HRID 841569Notes

Reaction equation

HRID 841569 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[C:20](=O)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2].ClCCl.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.C([BH3-])#N.[Na+]>CCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[CH:20]([NH:35][CH:32]4[CH2:34][CH2:33]4)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 69548870[2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester2×

Product 1

HCID 69548141[4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure G and using [2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester (Compound 14, 0.258 g, 0.68 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.266 g, 4.23 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20-25% ethyl acetate in hexane as the eluent , the title compound was obtained as a pale yellow oil (0.21 g, 73%).

Sources & evidence

ORD record
ord-cac1fed813c14ac79dcd781880c99bd9
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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