Hydrazine hydrate (1:1) → (+/-)-2-Amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile

HRID 2427274Notes

Reaction equation

HRID 2427274 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:33][C:15]2[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=3)[C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][C:22]=3[C:14]=2[CH2:13]1.O.NN>C(O)C.O1CCCC1.C(OCC)(=O)C>[NH2:3][CH:12]1[CH2:33][C:15]2[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=3)[C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][C:22]=3[C:14]=2[CH2:13]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59242740(+/-)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile

Product 1

HCID 59242745(+/-)-2-Amino-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrileYield 91.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (±)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(6-fluoro-pyridin-2-ylmethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (5.31 g, 12.2 mmol) in ethanol (15 mL)/tetrahydrofuran (85 mL). Add hydrazine monohydrate (4.43 ml, 91.2 mmol, 7.50 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ethyl acetate (150 ml), filter off white solids, wash the organic layer with 10% potassium carbonate twice, dry over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (3.42 g, 91%). LCMS 307.0 (M+1), 305.0 (M−1).

Workup

  1. filtrationfilter off white solids
  2. washwash the organic layer with 10% potassium carbonate twice
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-4e40de03d93642ccb5fb8789daa13aff
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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