2-Bromo-4-methylpyridine → (3-(1-Hydroxyethyl)-1-(5-(4-methylpyridin-2-yl)pyrimidin-2-yl)-1H-indol-6-yl)(morpholino)methanone

HRID 630537Notes

Reaction equation

HRID 630537 reaction equation
BrC1C=NC(N2C3C(=CC=C(C(N4CCOCC4)=O)C=3)C(CO)=C2)=NC=1.Br[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=1.FC1C=CC=CC=1C1C=NC(N2C3C(=CC=C(C(N4CCOCC4)=O)C=3)C(C=O)=C2)=NC=1.FC1C=CC=CC=1[C:74]1[CH:75]=[N:76][C:77]([N:80]2[C:88]3[C:83](=[CH:84][CH:85]=[C:86]([C:89]([N:91]4[CH2:96][CH2:95][O:94][CH2:93][CH2:92]4)=[O:90])[CH:87]=3)[C:82]([CH:97]([OH:99])[CH3:98])=[CH:81]2)=[N:78][CH:79]=1>>[OH:99][CH:97]([C:82]1[C:83]2[C:88](=[CH:87][C:86]([C:89]([N:91]3[CH2:92][CH2:93][O:94][CH2:95][CH2:96]3)=[O:90])=[CH:85][CH:84]=2)[N:80]([C:77]2[N:78]=[CH:79][C:74]([C:28]3[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=3)=[CH:75][N:76]=2)[CH:81]=1)[CH3:98]

Participants

5

Reactant 4

HCID 27340872-Bromo-4-methylpyridineHCID 1186660411-(5-(2-Fluorophenyl)pyrimidin-2-yl)-6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehydeHCID 118666263(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone2×HCID 118666316(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indol-6-yl)(morpholino)-methanone

Product 1

HCID 118666164(3-(1-Hydroxyethyl)-1-(5-(4-methylpyridin-2-yl)pyrimidin-2-yl)-1H-indol-6-yl)(morpholino)methanone

Procedure

(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone (intermediate 27c) was converted into a boronic ester that was subsequently reacted with 2-bromo-4-methylpyridine under Suzuki conditions. The resulting product was oxidized to the corresponding aldehyde and then submitted to a Grignard reaction analogously to the protocols 28a) and 28b), respectively. Light yellow solid. Yield: 70 mg

Sources & evidence

ORD record
ord-87961ad6e5d248be8c8ca2acc68079c2
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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