Sodium Carbonate → HCID 136068440, compound

HRID 2189230Notes

Reaction equation

HRID 2189230 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19][C@H:20]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]3)=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])=[N:9]2)=[CH:4][CH:3]=1.[CH3:32][O:33][CH2:34]/[CH:35]=[CH:36]/B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[OH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:8]1[N:7]=[C:6]([NH:19][C@H:20]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[CH2:21]2)[C:5]2[C:10](=[CH:11][C:2](/[CH:36]=[CH:35]/[CH2:34][O:33][CH3:32])=[CH:3][CH:4]=2)[N:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 136068466HCID 136068466, compound

Product 1

HCID 136068440HCID 136068440, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(S)-tert-Butyl 3-(7-bromo-2-(2-hydroxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.099 g, 0.20 mmol), trans-3-methoxy-1-propenylboronic acid pinacol ester (0.051 g, 0.23 mmol), Na2CO3 (0.066 g, 0.62 mmol), palladium tetrakistriphenyl phosphine (0.012 g, 0.011 mmol) was dissolved in a toluene (1 mL) and water (0.3 mL) and the mixture was degassed in a sealed tube. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was cooled and diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Further purification by silica column chromatography eluting with a gradient from 1% to 10% methanol in dichloromethane, gave the title compound as a yellow solid (0.071 g, 27%).

Workup

  1. customthe mixture was degassed in a sealed tube
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with water (50 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customFurther purification by silica column chromatography
  8. washeluting with a gradient from 1% to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-248347f4f1e54d83af262ad1b6dd8721
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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