Methanol → HCID 20780046, compound

HRID 1295850Notes

Reaction equation

HRID 1295850 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[N:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:9]2=[N:8][C:7]=1[C:26]([F:29])([F:28])[F:27])=O)C.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[N:17]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]2[C:6]([CH2:4][OH:3])=[C:7]([C:26]([F:29])([F:28])[F:27])[N:8]=[C:9]12

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 20780192HCID 20780192, compound

Product 1

HCID 20780046HCID 20780046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-(2,4-Dichloro-phenyl)-2-trifluoromethyl-8H-1,3a,8-triaza-cyclopenta[α]indene-3-carboxylic acid ethyl ester (490 mg, 1.11 mmol) in methylene chloride (20 mL), was added at 0° C. a toluene solution of DIBAL-H (5.55 mL, 5.55 mmol). After stirring at 0° C. for 75 min, the reaction mixture was cooled down to −78° C. and methanol (2.2 mL) was added dropwise, followed by additions of ground Na2SO4-10H2O (15.2 g) and celite (2.6 mL). The resulting mixture was warmed up to room temperature in 4 h. After filtration, the solvents were removed in vacuo to afford the title compound as an off white solid (443 mg, 100% yield). 1H NMR (CDCl3, 500 MHz) δ 8.00-7.93 (m, 1H), 7.65 (d, J=2.2 Hz, 1H0, 7.57 (d, J=7.4 Hz, 1H), 7.46 (dd, J=8.6, 2.3 Hz, 1H), 7.37-7.33 (m, 2H), 7.08-7.05 (m, 1H); Mass spec.: 400.02 (MH+).

Workup

  1. temperaturethe reaction mixture was cooled down to −78° C.
  2. temperatureThe resulting mixture was warmed up to room temperature in 4 h
  3. filtrationAfter filtration
  4. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ff32cd90dd144871abc0d8377dcb5e05
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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