Water → HCID 68784936, compound

HRID 2093590Notes

Reaction equation

HRID 2093590 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7](B(O)O)([CH3:9])=[CH2:8].Cl[C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][NH:27][C:28](=[O:49])[C:29]3[CH:34]=[CH:33][C:32]([C:35]4[O:36][C:37]5[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][C:41]([C:47]#[N:48])=[CH:40][C:38]=5[N:39]=4)=[CH:31][CH:30]=3)[CH2:22][CH2:21]2)[CH:17]=[CH:16][N:15]=1.O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(O)C>[C:47]([C:41]1[CH:42]=[C:43]([CH:44]([CH3:46])[CH3:45])[C:37]2[O:36][C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([NH:27][CH2:26][CH:23]4[CH2:24][CH2:25][N:20]([C:18]5[CH:17]=[CH:16][N:15]=[C:14]([C:7]([CH3:9])=[CH2:8])[N:19]=5)[CH2:21][CH2:22]4)=[O:49])=[CH:30][CH:31]=3)=[N:39][C:38]=2[CH:40]=1)#[N:48]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 25169790N-{[1-(2-Chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide

Product 1

HCID 68784936HCID 68784936, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Sodium carbonate (120 uL, 2M aqueous), isopropenylboronic acid (21 mg), and N-{[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (31 mg, EXAMPLE 7) were dissolved in toluene (2.1 ml), water (0.6 ml) and ethanol (0.3 ml). To this solution was added palladium tetrakis(triphenylphosphine) (10 mg). The mixture was heated to 150° C. for 25 min in a microwave reactor. Upon cooling, the mixture was then concentrated in vacuo, taken up in dichloromethane, and purified via flash chromatography on a Biotage Horizon, 25 M column, eluting with 10 column volumes of ethyl acetate to provide the title compound (19 mg, 61%). Mass spectrum (ESI) 521.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.5 Hz, 2H), 8.23 (d, J=6.2 Hz, 1H), 7.95 (d, J=8.0 Hz, 3H), 7.52 (s, 1H), 6.38 (d, J=6.2 Hz, 1H), 6.31 (t, J=6.0 Hz, 1H), 6.30 (s, 1H), 5.41 (s, 1H), 4.52 (d, J=8.7 Hz, 2H), 3.46 (m, 3H), 2.91 (t, J=12.4 Hz, 2H), 2.19 (s, 3H), 2.00 (m, 2H), 1.90 (d, J=12.2 Hz, 2H), 1.46 (d, J=7.0, 6H), 1.33 (m, 2H).

Workup

  1. temperatureUpon cooling
  2. concentrationthe mixture was then concentrated in vacuo
  3. custompurified via flash chromatography on a Biotage Horizon, 25 M column
  4. washeluting with 10 column volumes of ethyl acetate

Sources & evidence

ORD record
ord-3ae416a5af224897a7014aee075d59bd
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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