Sodium Carbonate → HCID 123152589, compound

HRID 510203Notes

Reaction equation

HRID 510203 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([S:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])(=[O:20])=[O:19])[CH:16]=3)[N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:43]1[CH:44]=[C:45]([NH:49][CH:50]([CH:59]([CH3:61])[CH3:60])[C:51]([NH:53][CH2:54][C:55]([F:58])([F:57])[F:56])=[O:52])[CH:46]=[N:47][CH:48]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:60][CH:59]([CH3:61])[CH:50]([NH:49][C:45]1[CH:44]=[C:43]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([S:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:20])[CH:16]=3)[N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])[CH:10]=2)[CH:48]=[N:47][CH:46]=1)[C:51](=[O:52])[NH:53][CH2:54][C:55]([F:58])([F:57])[F:56]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 894869872-[(5-bromopyridin-3-yl)amino]-3-methyl-N-(2,2,2-trifluoroethyl)butanamideHCID 123238556methyl 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-ylsulfonyl)propanoate

Product 1

HCID 123152589HCID 123152589, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To methyl 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-ylsulfonyl)propanoate 4-1c (3.26 mmol) was added aqueous sodium carbonate (4.89 ml, 9.79 mmol), 2-[(5-bromopyridin-3-yl)amino]-3-methyl-N-(2,2,2-trifluoroethyl)butanamide (1386 mg, 3.91 mmol) and Tetrakis (188 mg, 0.163 mmol). The reaction mixture was heated at 100° C. in a sealed vessel for 1 h. The reaction was cooled, quenched with water (50 mL), and product extracted with ethyl acetate (100 mL). The organic extract was dried over sodium sulfate, filtered and concentrated to oil. The oil was chromatographed on silica (100 g) using 50-100% ethyl acetate/hexanes to give the desired product 4-1d (1.1 g).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with water (50 mL), and product
  3. extractionextracted with ethyl acetate (100 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to oil
  8. customThe oil was chromatographed on silica (100 g)

Sources & evidence

ORD record
ord-5a6673b40548410d8accbbf0b300090d
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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