Morpholine → HCID 10194087, compound

HRID 7790Notes

Reaction equation

HRID 7790 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])[CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:24][O:23][C:9]1[CH:10]=[C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:7]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 103093892-[4-(6-Bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 10194087HCID 10194087, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
70 °C

Procedure

2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (150 mg, 0.39 mmol), morpholine (41 μL, 0.47 mmol), Pd2(dba)3 (8.2 mg, 0.0078 mmol), BINAP (9.8 mg, 0.016 mmol), and NaOtBu (53 mg, 0.55 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (4 mL) was added and the mixture was degassed with a stream of argon for 5 min. The tube was sealed and the mixture was heated to 70° C. for 18 h. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-methoxy-4-(6-morpholin-4-ylpyridin-2-yl)phenyl]-1,3-benzoxazole as an orange solid: 1H NMR (CDCl3, 300 MHz) δ 8.07–8.05 (d, 1H), 7.96–7.95 (m, 1H), 7.88 (s, 1H), 7.83–7.78 (m, 1H), 7.65–7.58 (m, 2H), 7.42–7.36 (m, 3H), 6.65–6.62 (d, 1H), 4.02 (s, 3H), 3.88–3.85 (t, 4H), 3.61–3.58 (t, 4H). MS (ESI) 388 (M+H)+.

Workup

  1. customevacuated
  2. additionToluene (4 mL) was added
  3. customthe mixture was degassed with a stream of argon for 5 min
  4. customThe tube was sealed
  5. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-5ee2516367524b7eaaf9585d456e1cfd
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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