Water → HCID 58710037, compound

HRID 2375943Notes

Reaction equation

HRID 2375943 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:33][C:17]3=[N:18][CH:19]=[C:20](Br)[C:21]([NH:22][C:23]4[CH:31]=[CH:30][C:26]5[N:27]=[CH:28][S:29][C:25]=5[CH:24]=4)=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:35](#[N:37])C>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.[Zn+2].[C-]#N.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]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:33][C:17]3=[N:18][CH:19]=[C:20]([C:35]#[N:37])[C:21]([NH:22][C:23]4[CH:31]=[CH:30][C:26]5[N:27]=[CH:28][S:29][C:25]=5[CH:24]=4)=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 598546031,1-Dimethylethyl 4-[4-(6-benzothiazolylamino)-5-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 58710037HCID 58710037, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To a mixture of 4-[4-(benzothiazol-6-ylamino)-5-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (20 mg, 0.038 mmol), DPPF (10.1 mg, 0.018 mmol), water (0.04 mL) and zinc cyanide (8.9 mg, 0.075 mmol) in acetonitrile-(4 mL) was added Pd2 dba3 (7.0 mg, 0.007 mmol) and the mixture was heated to reflux under N2 overnight. The reaction mixture was evaporated, and the crude product was purified by preparative TLC using 7% methanol in DCM as eluent to afford the title compound as light gray solid. 1H NMR (400 MHz, CDCl3): δ=8.98 (s, 1H), 8.22 (s, 1H), 8.10 (d, J=8.6 Hz, 1H), 7.78 (d, J=2.0 Hz, 1H), 7.36 (dd, J=8.6, 2.1 Hz, 1H), 6.95 (s, 1H), 5.93 (bs, 1H), 5.36 (s, 1H), 3.99-4.02 (m, 2H), 3.44 (t, J=5.7 Hz, 2H), 3.42 (d, J=4.9 Hz, 2H), 2.07-2.12 (m, 2H), 1.39 (s, 9H); MS (ES+): m/z 472.96 (100) [MH+]; HPLC: tR=3.25 min (ZQ2000, polar—5 min).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under N2 overnight
  3. customThe reaction mixture was evaporated
  4. customthe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-e7297a1e194e44e89d6fa93a0ad8b635
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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