Water → 1H-pyrrolo(2,3-b)pyridine-4-carbonitrile

HRID 497158

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.O.[NH4+].[Cl-].[NH4+].[OH-].[CH3:16][N:17](C=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2]>[NH:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:16]#[N:17])[C:3]=2[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (4.7 g, 19.3 mmol) of 4-Iodo-1H-pyrrolo[2,3-b]pyridine in degassed DMF (25 mL) was added Pd2(dba)3 (10 mg), dppf (15 mg), degassed H2O (2 mL) and Zn(CN)2 (1.4 g, 11.6 mmol). The mixture was stirred at 90° C. under nitrogen for 20 hr, then cooled to 70° C. and 75 mL of a 4:1:4 mixture of saturated NH4Cl:NH4OH:H2O was added. The mixture was stirred at 5° C. for 20 min. and the resulting precipitate filtered off, washed with 75 mL 4:1:5 mixture of saturated NH4Cl:NH4OH:H2O, 500 mL H2O and 100 mL toluene, then dried in vacuo to give 2.06 g (74%) 1H-Pyrrolo[2,3-b]pyridine-4-carbonitrile. MS (ES+): 143 [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ 6.65 (d, 1H, J=3.2), 7.56 (d, 1H, J=4.8 Hz), 7.84 (d, 1H, J=4.0 Hz), 8.40 (d, 1H, J=4.8 Hz).

Workup

temperaturecooled to 70° C.
stirringThe mixture was stirred at 5° C. for 20 min.
filtrationthe resulting precipitate filtered off
washwashed with 75 mL 4:1:5 mixture of saturated NH4Cl
dry with materialNH4OH:H2O, 500 mL H2O and 100 mL toluene, then dried in vacuo

Sources & evidence

ORD record: ord-168a8ade12a14fb9981eb872fe0c2ad9
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949563B2

Linked notes

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