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

HRID 51636Notes

Reaction equation

HRID 51636 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=O)[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])[CH3:2].ClCCl.[CH:31]1([NH2:34])[CH2:33][CH2:32]1.C([BH3-])#N.[Na+]>CCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(#N)C>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[CH:19]([NH:34][CH:31]4[CH2:33][CH2:32]4)[CH2:18][CH2:17][C:16]([CH3:24])([CH3:25])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])[CH3:2]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 129717122-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl ester2×

Product 1

HCID 129717134-[5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl]-2-fluoro-benzoic 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)-benzoic acid ethyl ester (Compound 9, 0.132 g, 0.3 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL) and sodium cyanoborohydride (0.18 g, 2.86 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.1 g, 82%).

Sources & evidence

ORD record
ord-4658538789364189a9a41d8c20441a00
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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