Sodium Carbonate → HCID 58529505, compound

HRID 1972786Notes

Reaction equation

HRID 1972786 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[N:5]2[C:10]=1[C:9]([NH2:11])=[N:8][CH:7]=[N:6]2.[CH2:24]([N:31]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35](B3OC(C)(C)C(C)(C)O3)[CH:36]=[CH:37]2)=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:24]([N:31]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([C:2]3[CH:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[N:5]4[C:10]=3[C:9]([NH2:11])=[N:8][CH:7]=[N:6]4)[CH:36]=[CH:37]2)=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 59232194HCID 59232194, compound

Product 1

HCID 58529505HCID 58529505, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 5-bromo-7-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (3.00 g, 7.51 mmol), 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (3.77 g, 11.3 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II) dichloromethane adduct (550 mg, 0.75 mmol) in degassed DME (50 mL) was added aqueous Na2CO3 solution (2 M, 11.3 mL). The reaction was heated (80° C.) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (75 mL) and water (75 mL) and the layers were separated. The aqueous phase was further extracted with ethyl acetate (2×75 mL). The combined organics were filtered to remove a fine precipitate, dried (Na2SO4), and concentrated. The crude material was purified by ISCO® chromatography using a gradient of 25 to 75% ethyl acetate in hexanes to afford 1.9 g (48%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.51 (s, 1 H), 7.85 (s, 1 H), 7.77 (dd, 1 H), 7.57-7.54 (m, 1 H), 7.35-7.25 (m, 5 H), 7.11 (dd, 1 H), 6.55 (s, 1 H), 5.63 (s, 2 H), 3.59 (t, 2 H), 2.88 (t, 2 H), 1.79-1.68 (m, 2 H), 1.58-1.48 (m, 2 H), 0.83 (s, 9 H), 0.00 (s, 6 H); ES-MS m/z 527.3 [M+H]+, HPLC RT (min) 3.62.

Workup

  1. temperaturecooled to rt
  2. customThe mixture was partitioned between ethyl acetate (75 mL) and water (75 mL)
  3. customthe layers were separated
  4. extractionThe aqueous phase was further extracted with ethyl acetate (2×75 mL)
  5. filtrationThe combined organics were filtered
  6. customto remove a fine precipitate
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-c4d2361b5513486396b2c575a99dcd55
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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