Hydrazine hydrate (1:1) → HCID 10114084, compound

HRID 2221288Notes

Reaction equation

[CH3:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[C:9]([C:27](=O)[C:28]([OH:30])=[O:29])=[CH:8]2)=[CH:4][CH:3]=1.O.NN.C[O-].[Na+]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=4)=[CH:13][CH:14]=3)[C:9]([CH2:27][C:28]([OH:30])=[O:29])=[CH:8]2)=[CH:32][CH:33]=1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 10138964HCID 10138964, compound

HCID 10942334Sodium Methoxide

Product 1

HCID 10114084HCID 10114084, compound

Procedure

The title compound was prepared from {1-(4-methylbenzyl)-5-[4-(trifluoromethoxy) phenyl]-1H-indol-3-yl}(oxo)acetic acid, hydrazine monohydrate and sodium methoxide according to the procedure described in Example 64. The product was obtained as a brown solid, mp: 62-63° C. Mass spectrum (−ESI, [M−H]−) m/z 438. 1HNMR (400 MHz, DMSO-d6): δ 7.79 (s, 1H), 7.75 (d, 2H, J=8.70 Hz), 7.50 (d, 1H, J=8.56 Hz), 7.42-7.39 (m, 4H), 7.12 (d, 2H, J=8.55 Hz), 7.11 (d, 2H, J=8.55 Hz), 5.34 (s, 2H), and 2.23 ppm (s, 3H). Elemental Analysis for C25H20F3NO3: Calculated: C, 68.33; H, 4.59; N, 3.19. Found: C, 68.00; H, 4.59; N, 3.40.

Workup

customThe product was obtained as a brown solid, mp: 62-63° C

Sources & evidence

ORD record: ord-a631b1d2e70d4f8980ce15729f544c46
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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