Malononitrile → 2-Amino-4-(5-bromo-pyridin-3-yl)-3-cyano-7-hydroxymethyl-4H-pyrrolo[2,3-h]chromene

HRID 490825Notes

Reaction equation

HRID 490825 reaction equation
[OH:1][CH2:2][N:3]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=O)[CH:17]=[N:18][CH:19]=1.[C:22](#[N:26])[CH2:23][C:24]#[N:25].N1CCCCC1>>[NH2:26][C:22]1[O:12][C:7]2[C:8]([CH:20]([C:16]3[CH:17]=[N:18][CH:19]=[C:14]([Br:13])[CH:15]=3)[C:23]=1[C:24]#[N:25])=[CH:9][CH:10]=[C:11]1[N:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=21

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 247769031-(Hydroxymethyl)-1H-indol-4-ol

Product 1

HCID 103407342-Amino-4-(5-bromo-pyridin-3-yl)-3-cyano-7-hydroxymethyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 1-hydroxymethyl-4-hydroxy-indole (66 mg, 0.4 mmol), 5-bromo-pyridine-3-carbaldehyde (75 mg, 0.4 mmol), malononitrile (27 mg, 0.4 mmol) and piperidine (0.02 mL, 0.2 mmol), similar to Example 16, to yield 60 mg (38%) of a white solid. 1H NMR (DMSO-d6): 8.58 (d, J=2.1 Hz, 1H), 8.48 (d, J=1.5 Hz, 1H), 7.78-7.76 (m, 1H), 7.45 (d, J=3.0 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.11 (brs, 2H), 6.77 (d, J=8.7 Hz, 1H), 6.49 (d, J=3.3 Hz, 2H), 5.49 (brs, 2H), 4.98 (s, 1H).

Sources & evidence

ORD record
ord-ffaf3ec31eb742719b692c4b399958e9
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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