tert-Butyl acrylate → HCID 59277621, compound

HRID 1362345Notes

Reaction equation

HRID 1362345 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].C(N(C(C)C)C(C)C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[C:7]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:6]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 22457514HCID 22457514, compound

Product 1

HCID 59277621HCID 59277621, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 2-(2-Amino-5-bromo-pyridin-3-yl)-propan-2-ol (200 mg, 0.86 mmol), tert-butyl acrylate (628 μL, 4.3 mmol) and (i-Pr)2EtN (452 μL, 2.6 mmol) in DMF (10 mL) was de-oxygenated with Ar for 30 min. The mixture was treated with Pd(OAc)2 (19.4 mg, 0.09 mmol) and P(o-tol)3 (51.7 mg, 0.18 mmol) then heated to 110° C. for 20 h. The hot mixture was filtered through a pad of celite. The filtrate was diluted with H2O (100 mL) then extracted with ethyl acetate (2×100 mL). The combined organic fractions were dried over MgSO4, and subjected to flash chromatography on silica gel using 50% ethyl acetate:hexanes. The appropriate fractions were collected and concentrated to yield a yellow crystalline solid. Yield: 153 mg (64%); 1H NMR (300 MHz, DMSO-d6) δ 8.09 (d, J=2.1 Hz, 1H), 7.65 (d, J=2.4 Hz, 1H), 7.45 (d, J=15.8 Hz, 1H), 6.69 (s, 2H), 6.32 (d, J=15.8 Hz, 1H), 5.53 (s, 1H), 1.52 (s, 6H), 1.48 (s, 9H); ESI MS m/z 279 [C15H22N2O3+H]+

Workup

  1. filtrationThe hot mixture was filtered through a pad of celite
  2. additionThe filtrate was diluted with H2O (100 mL)
  3. extractionthen extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated
  7. customto yield a yellow crystalline solid

Sources & evidence

ORD record
ord-31c538d5648c4a0f9057ea200fbb523b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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