Ammonia → 3-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amide

HRID 1505837Notes

Reaction equation

HRID 1505837 reaction equation
[NH3:1].C[O:3][C:4]([C:6]1[N:14]=[CH:13][C:12]2[NH:11][C:10]3[N:15]=[CH:16][C:17]([Br:19])=[CH:18][C:9]=3[C:8]=2[CH:7]=1)=O>CO>[NH3:11].[Br:19][C:17]1[CH:16]=[N:15][C:10]2[NH:11][C:12]3[CH:13]=[N:14][C:6]([C:4]([NH2:1])=[O:3])=[CH:7][C:8]=3[C:9]=2[CH:18]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58266719Methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c']dipyridine-6-carboxylate

Product 2

HCID 222AmmoniaHCID 582667993-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
140 °C

Procedure

In a steel bomb, a saturated solution of ammonia in methanol was prepared by passing gaseous ammonia through methanol (250 mL) then 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (14.0 g, 38.3 mol) was added. The vessel was sealed, then the reaction mixture was heated at 140° C. (15 bar) for 18 h. After this time, the reaction vessel was allowed to cool to ambient temperature then the reaction mixture was transferred to a round-bottomed flask and the solvent was removed in vacuo to afford a solid residue. The resultant solid residue was collected by filtration, washed with methanol (50 mL) and then dried to yield the desired product as a grey solid (9.47 g, 85%). 1H NMR (DMSO-D6, 400 MHz): 11.53 (s, 1H), 9.14 (d, J=2.3 Hz, 1H), 8.96 (d, J=1.1 Hz, 1H), 8.91 (d, J=1.1 Hz, 1H), 8.71 (d, J=2.3 Hz, 1H), 8.07 (s, 1H), 7.52 (s, 1H). LCMS (Method B): RT=2.49 min, M+H+=291/293.

Workup

  1. customThe vessel was sealed
  2. temperatureto cool to ambient temperature
  3. customthe reaction mixture was transferred to a round-bottomed flask
  4. customthe solvent was removed in vacuo
  5. customto afford a solid residue
  6. filtrationThe resultant solid residue was collected by filtration
  7. washwashed with methanol (50 mL)
  8. customdried

Sources & evidence

ORD record
ord-afe123680444470889ad9544a2d0571a
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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