3-Chlorophenol → (S)-2-(2-((3-Chlorophenoxy)methyl)morpholino)-1-(indolin-1-yl)ethanone

HRID 1524185Notes

Reaction equation

HRID 1524185 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][N:7]([CH2:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5][O:4]1.[Cl:21][C:22]1[CH:23]=[C:24](O)[CH:25]=[CH:26][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:21][C:22]1[CH:27]=[C:26]([CH:25]=[CH:24][CH:23]=1)[O:1][CH2:2][C@@H:3]1[CH2:8][N:7]([CH2:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5][O:4]1

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71061264(S)-2-(2-(Hydroxymethyl)morpholino)-1-(indolin-1-yl)ethanone

Product 1

HCID 71061724(S)-2-(2-((3-Chlorophenoxy)methyl)morpholino)-1-(indolin-1-yl)ethanoneYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 22s was synthesised by essentially the same procedure as compound 18s (Example 16), using compound 48 (Example 7; 55 mg, 0.2 mmol), 3-chlorophenol (39 mg, 0.3 mmol), triphenylphosphine (78 mg, 0.3 mmol), DEAD (0.05 ml, 0.3 mmol), and THF (1 ml). The crude residue was purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2) to afford the title compound as a colourless oil (51 mg; 65%). Analyses were performed on the free base, and the free base was converted to the HCl salt for testing.

Workup

  1. customThe crude residue was purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2)

Sources & evidence

ORD record
ord-9ec5416dc5914d2e8f7a2c2684a0e5e6
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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