Triethylamine → HCID 178435487, compound

HRID 1695690Notes

Reaction equation

HRID 1695690 reaction equation
[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[CH:20]=[C:19]([CH:21]=[CH2:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.[Pd].O>[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[CH:20]=[C:19](/[CH:21]=[CH:22]/[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 80271Tri-o-tolylphosphineHCID 178435485HCID 178435485, compound

Product 1

HCID 178435487HCID 178435487, compoundYield 22.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of (R)-indan-1-yl-(6-vinyl-4H-benzo[d][1,3]oxazin-2-yl)-amine (Example 134) (250 mg, 0.86 mmol), 3-bromopyridine (177 mg, 1.12 mmol), tri(o-tolyl)phosphine (21 mg, 0.07 mmol), triethylamine (261 mg, 2.58 mmol) and palladium actetate (7.73 mg, 0.034 mmol) in N,N-dimethylformamide (3 ml) was heated in a sealed tube at 100° C. for 3 h. The reaction mixture was poured into water (20 ml), extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with water (2×20 ml) and brine (20 ml), dried (magnesium sulfate) and evaporated. Further purification by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane) yielded the title compound as yellow solid (70 mg, 22%). MS (ISP): m/e=368.2 (M+H+); m.p. 132° C.

Workup

  1. extractionextracted with ethyl acetate (2×40 ml)
  2. washThe combined organic layers were washed with water (2×20 ml) and brine (20 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customFurther purification by flash chromatography (ethyl acetate/heptane)
  6. customon silica gel and crystallization (dichloromethane/heptane)

Sources & evidence

ORD record
ord-bd1c72216d5540f2b8a009fd58440b69
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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