3-Methoxyphenol → (S)-1-(Indolin-1-yl)-2-(2-((3-methoxyphenoxy)methyl)morpholino)ethanone

HRID 1524187Notes

Reaction equation

HRID 1524187 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.[CH3:21][O:22][C:23]1[CH:24]=[C:25](O)[CH:26]=[CH:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:12]1([C:10](=[O:11])[CH2:9][N:7]2[CH2:6][CH2:5][O:4][C@H:3]([CH2:2][O:1][C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:22][CH3:21])[CH:28]=3)[CH2:8]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 90073-MethoxyphenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71061264(S)-2-(2-(Hydroxymethyl)morpholino)-1-(indolin-1-yl)ethanone

Product 1

HCID 71062768(S)-1-(Indolin-1-yl)-2-(2-((3-methoxyphenoxy)methyl)morpholino)ethanoneYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Essentially the same procedure was used to make compound 24s as was used for compound 18s (Example 16), with compound 48 (Example 7; 55 mg, 0.2 mmol), 3-methoxyphenol (0.032 ml, 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 (60 mg; 78%). 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-9e58e5f6683b4d1c9c5e94fc00da00ff
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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