Water → Ethyl N-(8-bromo-2-methylimidazo[1,2-a]pyridin-7-yl)carbamate

HRID 1951353Notes

Reaction equation

HRID 1951353 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([CH3:16])[N:15]=[C:9]2[C:8]=1[Br:17].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:17][C:8]1[C:9]2[N:10]([CH:13]=[C:14]([CH3:16])[N:15]=2)[CH:11]=[CH:12][C:7]=1[NH:6][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 673603208-Bromo-2-methylimidazo[1,2-a]pyridin-7-amine

Product 1

HCID 67363252Ethyl N-(8-bromo-2-methylimidazo[1,2-a]pyridin-7-yl)carbamateYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of sodium bicarbonate (0.74 g, 8.81 mmol) and amine 18 (1.00 g, 4.42 mmol) in 50 mL of dry CH2Cl2 was treated over a period of fifteen minutes with ethyl chloroformate (2.40 g, 22.1 mmol). 4-Dimethylaminopyridine (0.08 g, 0.65 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. Then, water (25 mL) was added and the solution was extracted with CH2Cl2 (3×25 mL). The extracts were dried (Na2SO4), filtered and evaporated under vacuum. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford in order of elution: compound 19 (461 mg, yield: 35%); mp 137-138° C.; 1H NMR (200 MHz, CDCl3) δ 1.34 (t, 3H, J=7 Hz), 2.45 (s, 3H), 4.26 (q, 2H, J=7 Hz), 7.24 (brs, 1H), 7.31 (s, 1H), 7.81 (d, 1H, J=7.4 Hz), 7.92 (d, 1H, J=7.4 Hz); 13C NMR (100 MHz, DMSO-d6) δ 14.1, 14.4, 60.8, 102.5, 109.7, 111.3, 125.1, 133.3, 142.4, 143.0, 153.8. Starting material 18 (0.31 g, 31%).

Workup

  1. extractionthe solution was extracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified by chromatography
  6. customv/v) as eluent to afford in order of elution

Sources & evidence

ORD record
ord-ada2811d136c490e82ad859af4b64a21
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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