4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 6-Acetyl-3-fluoro-5,6-dihydro-2-[6-(4-morpholinyl)-3-pyridinyl]pyrido[3,2-c][1]benzazocine

HRID 2224306Notes

Reaction equation

HRID 2224306 reaction equation
[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[N:16]=[C:17](Cl)[C:18]([F:20])=[CH:19][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:30]2[CH:31]=[CH:32][C:33]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[N:34][CH:35]=2)O1.C(N1C2C=CC=CC=2C=CC2N=C(C3C=NC(OC)=CC=3)C(F)=CC=2C1)(=O)C>>[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[N:16]=[C:17]([C:30]3[CH:35]=[N:34][C:33]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[CH:32][CH:31]=3)[C:18]([F:20])=[CH:19][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 692911976-Acetyl-3-fluoro-5,6-dihydro-2-(6-methoxy-3-pyridinyl)-pyrido[3,2-c][1]benzazocineHCID 743934126-Acetyl-2-chloro-3-fluoro-5,6-dihydro-pyrido[3,2-c][1]benzazocine

Product 1

HCID 692911126-Acetyl-3-fluoro-5,6-dihydro-2-[6-(4-morpholinyl)-3-pyridinyl]pyrido[3,2-c][1]benzazocineYield 72.2%

Procedure

Compound 5B (20.5 mg, 72.2%) was prepared from 1D (20.0 mg, 0.066 mmol) and 5A (28.7 mg, 0.099 mmol) by a route analogous to that used for the preparation of 2B. HPLC Rt=2.336 min; LCMS Found: (M+H)+=431.

Sources & evidence

ORD record
ord-bd7cd6378d434181a451f9c839b5f0b0
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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