7-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1-benzopyran → HCID 71209444, compound

HRID 1912623Notes

Reaction equation

HRID 1912623 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[C:21]([O:25][C@@H:26]([C:31]1[C:32](I)=[C:33]2[CH:40]=[CH:39][N:38]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([F:48])=[C:44]([F:49])[CH:43]=3)[C:34]2=[N:35][C:36]=1[CH3:37])[C:27]([O:29]C)=[O:28])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C@@H:26]([C:31]1[C:32]([C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[F:1])[O:9][CH2:8][CH2:7][CH2:6]3)=[C:33]2[CH:40]=[CH:39][N:38]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([F:48])=[C:44]([F:49])[CH:43]=3)[C:34]2=[N:35][C:36]=1[CH3:37])[C:27]([OH:29])=[O:28])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 574162247-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1-benzopyranHCID 71209175HCID 71209175, compound

Product 1

HCID 71209444HCID 71209444, compound

Procedure

The title compound was prepared from 2-(7-fluorochroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate in a manner similar to that described in Example 87. The crude acid was recrystallized from an isopropanol/water mixture to give the title compound as a single isomer. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=7.36 (d, J=8.2 Hz, 1 H), 7.16-6.96 (m, 4 H), 6.68 (d, J=11.1 Hz, 1 H), 6.16 (s., 1 H), 5.57-5.45 (m, 2 H), 5.30 (d, J=15.2 Hz, 1 H), 4.26 (t, J=5.1 Hz, 2 H), 2.87-2.75 (m, 2 H), 2.71 (s, 3 H), 2.05 (d, J=4.9 Hz, 2 H), 1.02 (s, 9 H); LCMS (m/z) ES+=539 (M+1).

Workup

  1. customThe crude acid was recrystallized from an isopropanol/water mixture

Sources & evidence

ORD record
ord-7f373c1e3fc14681b0c46d4946ee9cb5
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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