Dimethylformamide → HCID 86670595, compound

HRID 401449Notes

Reaction equation

HRID 401449 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[C:13]([O:17][C:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1B(O)O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>CCOC(C)=O>[CH:11]([C:8]1[N:6]2[CH:7]=[C:2]([C:21]3[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[C:28]4[C:23]([CH:22]=3)=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 213456766-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde2×

Product 1

HCID 86670595HCID 86670595, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde (step 1 of Intermediate 1, 150 mg, 0.6729 mmol), 1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid (228 mg, 0.8742 mmol), dichlorobis(triphenylphosphine) palladium (II) (30 mg, 20% mmol) and 2M aqueous Na2CO3 (1 mL) were added to DMF (5 mL) and refluxed for 2 h. The reaction mixture was diluted with EtOAc and washed with water and brine. The solvent was evaporated to obtain solid residue, which was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 51%; 1H NMR (DMSO-d6; 300 MHz): δ 11.91 (s, 1H), 9.99 (s, 1H), 9.81 (s, 1H), 8.55 (s, 1H), 8.17 (dd, 1H, J=9.3, 1.8 Hz), 7.95 (d, 1H, J=9.3 Hz), 7.56 (d, 1H, J=7.8 Hz), 7.43 (d, 1H, J=8.4 Hz), 7.142 (t, 1H, J=7.2 Hz), 7.03 (m, 2H); MS: m/z 260 (M−1)+.

Workup

  1. temperaturerefluxed for 2 h
  2. washwashed with water and brine
  3. customThe solvent was evaporated
  4. customto obtain solid residue, which
  5. customwas purified by column chromatography (silica gel, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-7464e9d0934c4aaeaf95e86e26c041d9
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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